Crystalline (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt

Abstract

Provided herein are (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt forms, including crystalline forms, and methods of their preparation. Pharmaceutical compositions comprising a (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt are also provided, as are methods of using (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one tosylate salt to treat a disease or condition, such as a cancer.

What is claimed: 
     
       1. A crystalline tosylate salt of (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one having an X-ray powder diffraction pattern comprising peaks at 2θ angle degrees ±0.2 of 7.5, 20.1, and 24.1. 
     
     
       2. The crystalline tosylate salt of  claim 1 , having an X-ray powder diffraction pattern comprising peaks at 2θ angle degrees ±0.2 of 7.5, 15.1, 18.1, 20.1, 20.5, 22.6, and 24.1. 
     
     
       3. A crystalline tosylate salt of (8S,9R)-5-fluoro-8-(4-fluorophenyl)-9-(1-methyl-1H-1,2,4-triazol-5-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one exhibiting a solid state  13 C NMR spectrum with peaks at 143.2, 136.0, 131.8, 123.9, 112.2, 105.2, and 100.3 ppm ±0.2 ppm. 
     
     
       4. A pharmaceutical composition comprising the crystalline tosylate salt of  claim 1  and a pharmaceutically acceptable excipient. 
     
     
       5. A pharmaceutical composition comprising the crystalline tosylate salt of  claim 3  and a pharmaceutically acceptable excipient. 
     
     
       6. A pharmaceutical composition comprising the crystalline tosylate salt of  claim 2  and a pharmaceutically acceptable excipient.